JP2004522734A - Germicidal mixture - Google Patents
Germicidal mixture Download PDFInfo
- Publication number
- JP2004522734A JP2004522734A JP2002557209A JP2002557209A JP2004522734A JP 2004522734 A JP2004522734 A JP 2004522734A JP 2002557209 A JP2002557209 A JP 2002557209A JP 2002557209 A JP2002557209 A JP 2002557209A JP 2004522734 A JP2004522734 A JP 2004522734A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- halogen
- imidazole derivative
- alkyl
- valinamide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 230000002070 germicidal effect Effects 0.000 title claims description 7
- 241000233866 Fungi Species 0.000 claims abstract description 19
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 18
- -1 3,4-difluoromethylenedioxyphenyl group Chemical group 0.000 claims abstract description 16
- 150000002367 halogens Chemical class 0.000 claims abstract description 16
- XDEHMKQLKPZERH-BYPYZUCNSA-N (2s)-2-amino-3-methylbutanamide Chemical compound CC(C)[C@H](N)C(N)=O XDEHMKQLKPZERH-BYPYZUCNSA-N 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims abstract description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims abstract description 3
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
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Abstract
本発明は、A)式(I)[式中、R1およびR2は、ハロゲンまたはハロゲンもしくはアルキルにより置換されていてもよいフェニルを示すか、またはR1およびR2は、架橋C=C二重結合と一緒になって3,4-ジフルオロメチレンジオキシフェニル基を形成し、R3は、シアノまたはハロゲンを示し、R4は、ジアルキルアミノまたは2個のアルキル基を有していてもよいイソオキサゾール-4-イルを示す]で表されるイミダゾール誘導体;およびB)式(II)[式中、R’は、4位でハロゲンまたはC1-C4-アルキルもしくはC1-C4-アルコキシにより置換されているフェニル、1-ナフチルまたは2-ナフチル、または6位でハロゲンにより置換されているベンゾチアゾール-2-イルを示し、R”はC3-C4-アルキルを示す]で表されるバリンアミドを相乗的有効量で含む、殺菌性混合物に関する。本発明はまた、化合物(I)および(II)の混合物を用いて病原性菌類を防除する方法およびそのような混合物を製造するための化合物(I)および(II)の使用に関する。The invention relates to A) a compound of the formula (I) wherein R 1 and R 2 represent halogen or phenyl optionally substituted by halogen or alkyl, or R 1 and R 2 represent a bridged C = C Together with the double bond, a 3,4-difluoromethylenedioxyphenyl group is formed, R 3 represents cyano or halogen, and R 4 is a dialkylamino or a group having two alkyl groups. B) Formula (II) wherein R 'is halogen at the 4-position or C 1 -C 4 -alkyl or C 1 -C 4 -Phenyl, 1-naphthyl or 2-naphthyl substituted by alkoxy, or benzothiazol-2-yl substituted by halogen at the 6-position, and R ″ represents C 3 -C 4 -alkyl]. A fungicidal mixture containing a synergistically effective amount of the indicated valinamide. That. The present invention also relates to the use of Compound (I) and mixtures of a compound for the manufacture of a method and such a mixture for controlling phytopathogenic fungi using the (II) (I) and (II).
Description
【技術分野】
【0001】
本発明は、殺菌性混合物であって、
A) 式I:
【化1】
[式中、
R1およびR2は、ハロゲンまたはハロゲンもしくはC1-C4-アルキルにより置換されていてもよいフェニルであるか、またはR1およびR2は、架橋C=C二重結合と一緒になって3,4-ジフルオロメチレンジオキシフェニル基を形成し;
R3は、シアノまたはハロゲンであり、
R4は、ジ(C1-C4-アルキル)アミノまたは2個のC1-C4-アルキル基を有していてもよいイソオキサゾール-4-イルである]
で表されるイミダゾール誘導体;および
B) 式II:
【化2】
[式中、
R’は、4位でハロゲンまたはC1-C4-アルキルもしくはC1-C4-アルコキシにより置換されているフェニル、
1-ナフチルまたは2-ナフチル、または
6位でハロゲンにより置換されているベンゾチアゾール-2-イルであり;
R”は、C3-C4-アルキルである]
で表されるバリンアミド、
を相乗的有効量で含む、上記殺菌性混合物に関する。
【0002】
さらに、本発明は、化合物IおよびIIの混合物を用いて有害な菌類を防除する方法、並びにそのような混合物を調製するための化合物Iおよび化合物IIの使用に関する。
【背景技術】
【0003】
式Iで表されるイミダゾール誘導体類、その調製および有害な菌類に対するその作用は、文献により公知となっている(EP-A 298 196、WO-A 97/06171)。
【0004】
式IIで表されるバリンアミドおよびその調整方法は、EP-A-0 398 072、EP-A-0 610 764、DE-A-43 21 897、WO-A-96/07638およびJP-A 09/323984に記載されている。バリンアミドはさらに、DE 1 95 31 814に記載されているのと同様な方法で調製することができる。
【発明の開示】
【発明が解決しようとする課題】
【0005】
本発明の目的は、施用する活性化合物の総量が少ない、有害な菌類に対する作用を改良した混合物(相乗的混合物)を提供することであって、既知の化合物IおよびIIの施用率の減少並びに活性スペクトルの改良を目的とする。
【課題を解決するための手段】
【0006】
本発明者らは、この目的が、最初に定義した混合物により達成されることを発見した。さらに、本発明者らは、化合物Iおよび化合物IIを同時に、すなわち一緒に、または別々に施用するか、または化合物Iおよび化合物IIを順次施用すれば、個々の化合物をそれのみで施用するよりも、有害な菌類をよりよく防除できることを発見した。
【発明を実施するための最良の形態】
【0007】
式Iは特に、R1がハロゲン(特に塩素)であり、R2がトリル(特にp-トリル)である式Iで表されるイミダゾール誘導体を表す。
【0008】
同様に好ましいものとして、R4がジメチルアミノである式Iで表される化合物が挙げられる。
【0009】
その他に、特に好ましい化合物として、式Iaで表される化合物(一般名:シアゾファミド)が挙げられる。この化合物は、EP-A 298 196より知られている。
【化3】
好ましい化合物としてさらに、R1およびR2が、架橋C=C二重結合と一緒になって3,4-ジフルオロメチレンジオキシフェニル基を形成する式Iで表される化合物がさらに挙げられる。
【0010】
その他に好ましい化合物として、R4が3,5-ジメチルイソオキサゾール-4-イルである式Iで表される化合物が挙げられる。
【0011】
特に好ましい化合物として、式Ib:
【化4】
[式中、Xはハロゲンである]
で表される化合物が挙げられる。
【0012】
ハロゲンは、フッ素、塩素、臭素およびヨウ素を意味する。特に好ましいものとして、Xが臭素または塩素である、式Ibで表される化合物が挙げられる。
【0013】
好ましいものとして、アミノ酸部分がS型である式II’で表される化合物が挙げられる。この化合物は、式II’:
【化5】
に対応する。
【0014】
別の好ましい実施形態では、基R’に隣接する炭素がR型である式II’で表される化合物が用いられる。この化合物は、式II”:
【化6】
に対応する。
【0015】
式II’およびII”は特に、置換基がそれぞれの場合に下記表の一行に対応する、式IIaおよびIIbで表されるバリンアミドを示す:
【表1】
特に好ましいものとして、化合物II-3、II-9および化合物II-15:
【化7】
が挙げられる
化合物II-1〜II-15については、式II’の構造が好ましい。
【0016】
特に好ましいものとして、第二成分としてII-3(一般名:イプロバリカルブ)、II-9またはII-15を含む、式Iaで表される化合物の混合物が挙げられる。
【0017】
混合物を調製するときに、純粋な活性化合物IおよびIIを用いることが好ましく、そこに有害な菌類またはその他の害虫(例えば昆虫、クモ形類動物または線虫)に対して活性のある別の化合物、または他の除草活性化合物若しくは生長調節活性化合物または肥料を混合することができる。
【0018】
化合物IおよびIIの混合物、または同時に、一緒にもしくは別々に施用される化合物IおよびIIは、広い範囲の植物病原菌(特に子嚢菌類、担子菌類、藻菌類および不完全菌類)に対して顕著な活性を示す。これらのものの中には、全身に作用し、そのため葉および土壌に作用する殺菌剤としても用いることができるものがある。
【0019】
これらは、様々な作物、例えば綿、野菜種(例えばキュウリ、豆、トマト、ジャガイモおよびウリ)、オオムギ、グラス、カラスムギ、バナナ、コーヒー、トウモロコシ、果実種、コメ、ライ麦、大豆、ブドウ、コムギ、観賞植物、サトウキビ、および様々の種子などの種々の穀物において、多数の菌類を防除するために特に重要である。
【0020】
これらは、次の植物病原菌類を防除するのに特に適している:穀類のうどんこ病菌(Erysiphe graminis)(うどんこ病)、ウリ科植物のうどんこ病菌(Erysiphe cichoracearum)およびウリ科のうどんこ病菌(Sphaerotheca fuliginea)、リンゴのうどんこ病菌(Podosphaera leucotricha)、ブドウのうどんこ病菌(Uncinula necator)、穀物のさび病菌(Puccinia species)、綿、コメおよび芝生のリゾクトニア菌(Rhizoctonia species)、穀物およびサトウキビの黒穂菌(Ustilago species)、リンゴの黒星病菌(Venturia inaequalis)(黒星病)、穀物の褐条葉枯病菌(Helminthosporium species)、コムギのセプトリア・ノドラム(Septoria nodorum)、イチゴ、野菜、観賞植物およびブドウのボトリチス・シネレア菌(Botrytis cinerea)(灰色かび病)、落花生類のセロスポラ・アラキジコラ(Cercospora arachidicola)、コムギおよびオオムギのコムギ眼紋病菌(Pseudocercosporella herpotrichoides)、コメのイネいもち病菌(Pyricularia oryzae)、ジャガイモおよびトマトの胴枯れ病菌(Phytophthora infestans)、ブドウのべと病菌(Plasmopara viticola)、ホップおよびキュウリのシュードペロナスポラ菌(Pseudoperonaspora species)、野菜および果物のアルタナリア菌(Alternaria species)、バナナのマイコスファエレラ菌(Mycosphaerella species)およびまたフザリウム菌(Fusarium)およびバーティシリウム菌(Verticillium species)。
【0021】
さらに、それらは、例えばペシロミセス・ヴァリオテイ(Paecilomyces variotii)に対する物質の保護(例えば木の保護)のために用いることができる。
【0022】
化合物IおよびIIは、同時に、すなわち一緒若しくは別々のいずれかに、または順次に施用することができ、別々に施用する場合の順番は、一般に防除測定の結果に影響を及ぼさない。
【0023】
化合物IおよびIIは、通常20:1〜1:20、特に10:1〜1:10、好ましくは5:1〜1:5の重量比で用いる。
【0024】
所望する効果の種類に応じて、本発明の混合物の施用率は、特に農業栽培下の区域の場合、0.01〜8kg/ha、好ましくは0.1〜5kg/ha、特に0.1〜3.0 kg/haである。
【0025】
化合物Iの施用率は、0.01〜1kg/ha、好ましくは0.05〜0.5 kg/ha、特に0.05〜0.3 kg/haである。
【0026】
化合物IIの施用率は、対応して、0.01〜1kg/ha、好ましくは0.02〜0.5 kg/ha、特に0.05〜0.3 kg/haである。
【0027】
種子の処理のための混合物の施用率は、一般に、種子1kg当たり0.001〜250 g、好ましくは0.01〜100 g、特に0.01〜50 gである。
【0028】
有害な植物病原菌類を防除する場合、化合物IおよびIIの別々若しくは一緒での施用または化合物IおよびIIの混合物の施用は、植物の播種前または播種後、または植物発生前または植物発生後に、種子、植物または土壌にスプレーするかまたはダスティングすることにより達成される。
【0029】
本発明の殺菌性相乗的混合物、または化合物IおよびIIは、例えば即時スプレー可能な溶液、粉末および懸濁液または高濃度の水性、油性若しくはその他の懸濁液、分散液、エマルション、油分散液、ペースト、ダスト、散布用物質または顆粒の形態に製剤することが可能であり、またスプレー、噴霧、ダスティング、散布および散水により施用することができる。使用形態は、意図する目的による;いずれの場合であっても、本発明の混合物の分散をできるだけ細かく均一にするべきである。
【0030】
製剤は、それ自体知られた方法、例えば溶媒および/または担体を添加することにより調製する。不活性添加物(例えば乳化剤または分散剤など)を製剤と混合することが通例である。
【0031】
適当な界面活性剤は、芳香族スルホン酸類(例えばリグノスルホン酸、フェノールスルホン酸、ナフタレンスルホン酸およびジブチルナフタレンスルホン酸)および脂肪酸類のアルカリ金属塩類、アルカリ土類金属塩類およびアンモニウム塩類、アルキルスルホネート類およびアルキルアリールスルホネート類、アルキル、ラウリルエーテルおよび脂肪アルコールサルフェート、および硫酸化ヘキサデカノール類、ヘプタデカノール類およびオクタデカノール類の塩類、または脂肪アルコールグリコールエーテル類の塩類、スルホン化ナフタレンおよびその誘導体とホルムアルデヒドとの縮合物、ナフタレンまたはナフタレンスルホン酸類とフェノールおよびホルムアルデヒドとの縮合物、ポリオキシエチレンオクチルフェノールエーテル、エトキシル化イソオクチルフェノール、オクチルフェノールまたはノニルフェノール、アルキルフェニルポリグリコールエーテル類、トリブチルフェニルポリグリコールエーテル類、アルキルアリールポリエーテルアルコール類、イソトリデシルアルコール、脂肪アルコール/エチレンオキシド縮合物、エトキシル化ヒマシ油、ポリオキシエチレンアルキルエーテル類またはポリオキシプロピレンアルキルエーテル類、ラウリルアルコールポリグリコールエーテルアセテート類、ソルビトールエステル類、リグノ亜硫酸廃液類またはメチルセルロースである。
【0032】
粉剤、散布用物質およびダストは、化合物IもしくはII、または化合物IおよびIIの混合物を固体担体とともに混合するか、または一緒に粉砕することにより調製することができる。
【0033】
顆粒(例えばコーティングした顆粒、含浸させた顆粒、または均一な顆粒)は、通常、活性化合物を固体担体と結合させることにより調製する。
【0034】
充填剤または固体担体は、例えば、鉱物土、例えばシリカ類(例えばシリカゲル)、シリケート、タルク、カオリン、石灰石、石灰、チョーク、粘土、黄土、クレー、ドロマイト、珪藻土、硫酸カルシウム、硫酸マグネシウム、酸化マグネシウム、粉末合成物質、および肥料(例えば硫酸アンモニウム、リン酸アンモニウム、硝酸アンモニウム、尿素)、並びに野菜由来の生成物、例えば穀類ミール、樹皮ミール、木のミールおよび殻のミール、セルロース粉末、または他の固体担体である。
【0035】
製剤は一般に、0.1〜95重量%、好ましくは0.5〜90重量%の化合物IおよびIIのうちの一つ、または化合物IおよびIIの混合物を含む。活性化合物を(NMRスペクトルまたはHPLCにしたがって)純度90%〜100%、好ましくは95%〜100%で用いる。
【0036】
化合物IもしくはIIまたは混合物、または対応する製剤を、有害な菌類、その生育環境または該菌類が存在しないように保たれるべき植物、種子、土壌、区域、物質若しくは空間を、殺菌的に有効な量の混合物または別々に施用する場合は化合物IおよびIIにより処理することにより施用する。
【0037】
施用は、有害な菌類による感染の前または後に行うことができる。
【実施例】
【0038】
使用例
本発明の混合物の相乗的活性を、以下の実験により示した:
別々または一緒に、活性化合物を、63重量%のシクロヘキサノンと27重量%の乳化剤の混合物中で10%エマルションとして製剤し、所望の濃度になるまで水で希釈した。
【0039】
評価は、感染した葉の区域をパーセントで測定することにより行った。これらのパーセンテージを効力に変換した。効力(W)を、次のアボットの式を用いて計算した:
W = (1 - α)・100/β
αは、処理した植物の菌類感染(%)に対応し、
βは、未処理の植物(対照)の菌類感染(%)に対応する。
【0040】
効力0とは、処理した植物の感染レベルが未処理の対照植物の感染レベルに相当することを意味し;効力100とは、処理した植物が感染しなかったことを意味する。
【0041】
活性化合物の混合物の予想効力を、コルビーの式[R.S. Colby, Weeds 15, 20-22 (1967)]を用いて決定し、測定効力と比較した。
【0042】
コルビーの式: E = x + y - x・y/100
Eは、活性化合物AおよびBを濃度aおよびbで用いた場合の混合物の予想効力であり、未処理対照の%で表し、
xは、活性化合物Aを濃度aで用いた場合の効力であり、未処理対照の%で表し、
yは、活性化合物Bを濃度bで用いた場合の効力であり、未処理対照の%で表す。
【0043】
使用例:枯病菌( Phytophthora infestans )を原因とするトマトの枯病に対する保護活性
栽培品種「Groβe Fleischtomate St. Pierre」の鉢植えの葉に、10%の活性化合物、85%のシクロヘキサノンおよび5%の乳化剤を含む保存液から調製した水性調製液を流れ出すまでスプレーした。翌日、葉に、1ml当り0.25x106胞子の濃度の枯病菌(Phytophthora infestans)の遊走子冷水懸濁液を接種した。この植物を次に18〜20℃の水蒸気で飽和させたチェンバーに放置した。6日後、未処理であるが感染させた対照植物の枯病は、感染が視覚的に%で観察できる範囲まで広がった。
【表2】
【表3】
*)コルビーの式を用いて計算した。
【0044】
試験結果より、全ての混合比について、測定効力は、コルビーの式を用いて予め計算したものよりも高いことが示されている。【Technical field】
[0001]
The invention relates to a bactericidal mixture,
A) Formula I:
Embedded image
[Where,
R 1 and R 2 are halogen or phenyl optionally substituted by halogen or C 1 -C 4 -alkyl, or R 1 and R 2 together with a bridged CCC double bond Forming a 3,4-difluoromethylenedioxyphenyl group;
R 3 is cyano or halogen;
R 4 is di (C 1 -C 4 -alkyl) amino or isoxazol-4-yl optionally having two C 1 -C 4 -alkyl groups.
An imidazole derivative represented by the formula:
B) Formula II:
Embedded image
[Where,
R ′ is phenyl substituted at the 4-position by halogen or C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy,
1-naphthyl or 2-naphthyl, or benzothiazol-2-yl substituted at position 6 by halogen;
R "is, C 3 -C 4 - alkyl]
Valinamide represented by
In a synergistically effective amount.
[0002]
Furthermore, the invention relates to a method for controlling harmful fungi with a mixture of compounds I and II, and to the use of compounds I and II for preparing such mixtures.
[Background Art]
[0003]
The imidazole derivatives of the formula I, their preparation and their action against harmful fungi are known from the literature (EP-A 298 196, WO-A 97/06171).
[0004]
Valinamide represented by formula II and its preparation method are described in EP-A-0 398 072, EP-A-0 610 764, DE-A-43 21 897, WO-A-96 / 07638 and JP-A 09 / 323984. Valinamide can also be prepared in a similar manner as described in DE 195 31 814.
DISCLOSURE OF THE INVENTION
[Problems to be solved by the invention]
[0005]
It is an object of the present invention to provide mixtures (synergistic mixtures) with a reduced total amount of active compounds to be applied, which have an improved action against harmful fungi, with reduced application rates and activity of known compounds I and II. The aim is to improve the spectrum.
[Means for Solving the Problems]
[0006]
We have found that this object is achieved by the mixtures defined at the outset. Furthermore, the present inventors have found that applying compound I and compound II simultaneously, i.e. together or separately, or applying compound I and compound II sequentially, rather than applying the individual compounds alone. And found that it could better control harmful fungi.
BEST MODE FOR CARRYING OUT THE INVENTION
[0007]
Formula I particularly represents an imidazole derivative of the formula I in which R 1 is halogen (especially chlorine) and R 2 is tolyl (especially p-tolyl).
[0008]
Also preferred are compounds of formula I wherein R 4 is dimethylamino.
[0009]
Other particularly preferred compounds include compounds represented by the formula Ia (generic name: cyazofamid). This compound is known from EP-A 298 196.
Embedded image
Further preferred compounds further include those compounds of formula I wherein R 1 and R 2 together with a bridging CCC double bond form a 3,4-difluoromethylenedioxyphenyl group.
[0010]
Other preferred compounds include compounds of formula I wherein R 4 is 3,5-dimethylisoxazol-4-yl.
[0011]
Particularly preferred compounds include compounds of formula Ib:
Embedded image
[Wherein X is halogen]
The compound represented by these is mentioned.
[0012]
Halogen means fluorine, chlorine, bromine and iodine. Particularly preferred are the compounds of formula Ib, wherein X is bromine or chlorine.
[0013]
Preferred are compounds of formula II 'where the amino acid moiety is of the S type. This compound has the formula II ':
Embedded image
Corresponding to
[0014]
In another preferred embodiment, compounds of the formula II ′ in which the carbon adjacent to the group R ′ is in the R-form are used. This compound has the formula II ":
Embedded image
Corresponding to
[0015]
The formulas II ′ and II ″ in particular denote valinamides of the formulas IIa and IIb, in which the substituents in each case correspond to one row of the following table:
[Table 1]
Particularly preferred are compounds II-3, II-9 and compound II-15:
Embedded image
For compounds II-1 to II-15, the structure of formula II ′ is preferred.
[0016]
Particularly preferred are mixtures of the compounds of the formula Ia, which contain II-3 (generic name: iprovalicarb), II-9 or II-15 as second component.
[0017]
In preparing the mixtures, it is preferable to use the pure active compounds I and II, in which another compound which is active against harmful fungi or other pests (eg insects, arachnids or nematodes) Or other herbicidally active compounds or growth-regulating active compounds or fertilizers.
[0018]
Mixtures of compounds I and II, or compounds I and II applied simultaneously, together or separately, are remarkable against a wide range of phytopathogenic fungi, especially ascomycetes, basidiomycetes, algae and incomplete fungi Show activity. Some of these act systemically and can therefore also be used as fungicides acting on leaves and soil.
[0019]
These include various crops, such as cotton, vegetable species (eg, cucumber, beans, tomatoes, potatoes and cucumber), barley, grass, oats, bananas, coffee, corn, fruit species, rice, rye, soy, grape, wheat, Of particular importance in controlling various fungi in various cereals, such as ornamental plants, sugar cane, and various seeds.
[0020]
They are particularly suitable for controlling the following phytopathogenic fungi: cereal powdery mildew (Erysiphe graminis) (mildew), cucurbite powdery mildew (Erysiphe cichoracearum) and cucurbite powdery mildew Disease fungi (Sphaerotheca fuliginea), apple powdery mildew (Podosphaera leucotricha), grape powdery mildew (Uncinula necator), cereal rust (Puccinia species), cotton, rice and lawn Rhizoctonia species, cereals and Ustilago species of sugarcane, Venturia inaequalis of apple (scab), Helminthosporium species of cereals, Septoria nodorum of wheat, strawberries, vegetables, ornamental plants And grape Botrytis cinerea (grey mold), peanut Cercospora arachidic ola), Pseudocercosporella herpotrichoides on wheat and barley, Pyricularia oryzae on rice, Phytophthora infestans on potatoes and tomatoes, downy mildew on grape (Plasmopara viticola), hops and Pseudoperonaspora species in cucumber, Alternaria species in vegetables and fruits, Mycosphaerella species in bananas and also Fusarium and Verticillium species.
[0021]
Furthermore, they can be used, for example, for the protection of substances against Paecilomyces variotii (for example for the protection of trees).
[0022]
Compounds I and II can be applied simultaneously, ie either together or separately, or sequentially, the order in which they are separately applied generally does not affect the results of the control measurement.
[0023]
Compounds I and II are usually used in a weight ratio of 20: 1 to 1:20, in particular 10: 1 to 1:10, preferably 5: 1 to 1: 5.
[0024]
Depending on the type of effect desired, the application rates of the mixtures according to the invention are in the range of 0.01 to 8 kg / ha, preferably 0.1 to 5 kg / ha, especially 0.1 to 3.0 kg / ha, especially in areas under agricultural cultivation. .
[0025]
The application rates of compound I are from 0.01 to 1 kg / ha, preferably from 0.05 to 0.5 kg / ha, in particular from 0.05 to 0.3 kg / ha.
[0026]
The application rates of compound II are correspondingly between 0.01 and 1 kg / ha, preferably between 0.02 and 0.5 kg / ha, in particular between 0.05 and 0.3 kg / ha.
[0027]
The application rates of the mixture for the treatment of seed are generally from 0.001 to 250 g, preferably from 0.01 to 100 g, in particular from 0.01 to 50 g, per kg of seed.
[0028]
When controlling harmful phytopathogenic fungi, the application of compounds I and II separately or together or of a mixture of compounds I and II may be carried out before or after sowing of the plant, or before or after the emergence of the plant. By spraying or dusting the plant or soil.
[0029]
The germicidal synergistic mixtures according to the invention, or the compounds I and II, can be used, for example, in solutions, powders and suspensions which are ready for immediate spraying or in highly concentrated aqueous, oily or other suspensions, dispersions, emulsions, oil dispersions. It can be formulated in the form of pastes, dusts, dusting substances or granules and can be applied by spraying, spraying, dusting, dusting and watering. The use form depends on the intended purpose; in each case, the distribution of the mixtures according to the invention should be as fine and uniform as possible.
[0030]
The formulations are prepared in a manner known per se, for example by adding solvents and / or carriers. It is customary to mix inert additives (such as emulsifiers or dispersants) with the formulation.
[0031]
Suitable surfactants include aromatic sulfonic acids (eg, lignosulfonic acid, phenolsulfonic acid, naphthalenesulfonic acid and dibutylnaphthalenesulfonic acid) and alkali metal, alkaline earth metal and ammonium salts of fatty acids, alkyl sulfonates. And alkylaryl sulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexadecanols, heptadecanols and octadecanols, or salts of fatty alcohol glycol ethers, sulfonated naphthalene and derivatives thereof With formaldehyde, condensates of naphthalene or naphthalene sulfonic acids with phenol and formaldehyde, polyoxyethylene octyl phenol ether, Toxylated isooctylphenol, octylphenol or nonylphenol, alkylphenyl polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol / ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene Alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetates, sorbitol esters, lignosulfite waste liquors or methylcellulose.
[0032]
Powders, materials for spreading and dusts can be prepared by mixing or grinding together compound I or II, or a mixture of compounds I and II, with a solid carrier.
[0033]
Granules, for example coated granules, impregnated granules or homogeneous granules, are usually prepared by combining the active compounds with a solid carrier.
[0034]
Fillers or solid carriers include, for example, mineral earths such as silicas (eg, silica gel), silicates, talc, kaolin, limestone, lime, chalk, clay, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide. , Powdered synthetics, and fertilizers (eg, ammonium sulfate, ammonium phosphate, ammonium nitrate, urea), and products derived from vegetables, such as cereal meal, bark meal, tree meal and shell meal, cellulose powder, or other solid carriers It is.
[0035]
The formulations generally comprise between 0.1 and 95% by weight, preferably between 0.5 and 90% by weight, of one of the compounds I and II or a mixture of the compounds I and II. The active compounds are employed in a purity of from 90% to 100% (according to NMR spectrum or HPLC), preferably 95% to 100%.
[0036]
Compounds I or II or mixtures, or the corresponding preparations, can be used to disinfect plants, seeds, soil, areas, substances or spaces in which harmful fungi, their growth environment or the fungi are to be kept free. It is applied by treatment with the compounds I and II in the amount of the mixture or, if applied separately.
[0037]
Application can take place before or after infection by harmful fungi.
【Example】
[0038]
Use examples The synergistic activity of the mixtures according to the invention has been demonstrated by the following experiments:
The active compounds, separately or together, were formulated as 10% emulsions in a mixture of 63% by weight of cyclohexanone and 27% by weight of emulsifier and diluted with water to the desired concentration.
[0039]
Evaluation was performed by measuring the area of infected leaves in percent. These percentages were converted to potency. The potency ( W ) was calculated using the following Abbott formula:
W = (1-α) ・ 100 / β
α corresponds to the fungal infection (%) of the treated plant,
β corresponds to the fungal infection (%) of the untreated plant (control).
[0040]
A potency of 0 means that the infection level of the treated plants corresponds to the infection level of the untreated control plants; a potency of 100 means that the treated plants were not infected.
[0041]
The expected potency of the mixture of active compounds was determined using Colby's formula [RS Colby, Weeds 15 , 20-22 (1967)] and compared to the measured potency.
[0042]
Colby formula: E = x + y-x ・ y / 100
E is the expected potency of the mixture when active compounds A and B were used at concentrations a and b, expressed as% of untreated control,
x is the potency when active compound A was used at concentration a, expressed as% of untreated control,
y is potency when active compound B is used at concentration b and is expressed as% of untreated control.
[0043]
Usage example: Protective activity against tomato blight caused by blight fungus ( Phytophthora infestans ) 10% active compound, 85% cyclohexanone and 85% on potted leaves of cultivar "Groβe Fleischtomate St. Pierre" Aqueous preparations prepared from stock solutions containing 5% emulsifier were sprayed out. The next day, the leaves were inoculated with a zoospore cold water suspension of Phytophthora infestans at a concentration of 0.25 × 10 6 spores / ml. The plants were then left in a chamber saturated with steam at 18-20 ° C. After 6 days, the blight of untreated but infected control plants had spread to the extent that infection could be visually observed in%.
[Table 2]
[Table 3]
*) Calculated using Colby's equation.
[0044]
The test results show that for all mixing ratios, the measured efficacy is higher than that previously calculated using Colby's formula.
Claims (10)
A) 式I:
R1およびR2は、ハロゲンまたはハロゲンもしくはC1-C4-アルキルにより置換されていてもよいフェニルであるか、またはR1およびR2は、架橋C=C二重結合と一緒になって3,4-ジフルオロメチレンジオキシフェニル基を形成し;
R3は、シアノまたはハロゲンであり、
R4は、ジ(C1-C4-アルキル)アミノまたは2個のC1-C4-アルキル基を有していてもよいイソオキサゾール-4-イルである]
で表されるイミダゾール誘導体;および
B) 式II:
R’は、4位でハロゲンまたはC1-C4-アルキルもしくはC1-C4-アルコキシにより置換されているフェニル、
1-ナフチルまたは2-ナフチル、または
6位でハロゲンにより置換されているベンゾチアゾール-2-イルであり;
R”は、C3-C4-アルキルである]
で表されるバリンアミド、
を相乗的有効量で含む、上記殺菌性混合物。A germicidal mixture,
A) Formula I:
R 1 and R 2 are halogen or phenyl optionally substituted by halogen or C 1 -C 4 -alkyl, or R 1 and R 2 together with a bridged CCC double bond Forming a 3,4-difluoromethylenedioxyphenyl group;
R 3 is cyano or halogen;
R 4 is di (C 1 -C 4 -alkyl) amino or isoxazol-4-yl optionally having two C 1 -C 4 -alkyl groups.
An imidazole derivative represented by the formula:
B) Formula II:
R ′ is phenyl substituted at the 4-position by halogen or C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy,
1-naphthyl or 2-naphthyl, or benzothiazol-2-yl substituted at position 6 by halogen;
R "is, C 3 -C 4 - alkyl]
Valinamide represented by
A bactericidal mixture as described above, comprising a synergistically effective amount of
に対応する、請求項1に記載の殺菌性混合物。The imidazole derivative I has the formula Ib:
The germicidal mixture according to claim 1, corresponding to
有害な菌類、その生育環境、またはそれらが存在しないように保たれるべき植物、種子、土壌、区域、物質若しくは空間を、請求項1に記載の式Iで表されるイミダゾール誘導体および請求項1に記載の式IIで表されるバリンアミドで処理するステップを含む、上記方法。A method for controlling harmful fungi,
The imidazole derivative represented by the formula I according to claim 1, wherein the harmful fungus, its growth environment, or a plant, seed, soil, area, substance, or space to be kept free from the harmful fungus, and the imidazole derivative. The method as described above, comprising the step of treating with a valinamide represented by the formula II described in the above.
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DE10102835 | 2001-01-22 | ||
PCT/EP2002/000497 WO2002056690A1 (en) | 2001-01-22 | 2002-01-19 | Fungicide mixtures |
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EP (1) | EP1355531B1 (en) |
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CN103125509A (en) * | 2013-04-06 | 2013-06-05 | 海利尔药业集团股份有限公司 | Sterilizing combination containing benthiavalicarb-isopropyl and cyazofamid |
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CA1339133C (en) * | 1987-03-13 | 1997-07-29 | Rikuo Nasu | Imidazole compounds and biocidal composition comprising the same for controlling harmful organisms |
DE3915755A1 (en) | 1989-05-13 | 1990-11-29 | Bayer Ag | FUNGICIDAL AGENTS AND SUBSTITUTED AMINO ACID DERIVATIVES AND THE PRODUCTION THEREOF |
US5504109A (en) | 1989-05-13 | 1996-04-02 | Bayer Aktiengesellschaft | Susbstituted amino acid amide derivatives their preparation and use |
DE4304172A1 (en) | 1993-02-12 | 1994-08-25 | Bayer Ag | Fungicidal active ingredient combinations |
DE4321206A1 (en) | 1993-06-25 | 1995-01-05 | Bayer Ag | Fungicidal active ingredient combinations |
DE4321897A1 (en) * | 1993-07-01 | 1995-01-12 | Hoechst Schering Agrevo Gmbh | Substituted amino acid derivatives, processes for their preparation, compositions comprising them, and their use |
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DE19531814A1 (en) | 1995-08-30 | 1997-03-06 | Basf Ag | New isomeric N-substd. valine naphthyl-ethyl amide cpds. |
RU2170735C2 (en) | 1995-08-10 | 2001-07-20 | Байер Аг | Derivatives of halogen-substituted benzimidazole and their acid-additive salts, intermediate compounds and fungicide agent |
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US5577976A (en) | 1995-08-31 | 1996-11-26 | General Motors Corporation | Power transmission |
JPH09323984A (en) | 1996-06-04 | 1997-12-16 | Kumiai Chem Ind Co Ltd | Amino acid amide derivative and germicide for agriculture and horticulture |
DE19716256A1 (en) | 1997-04-18 | 1998-10-22 | Bayer Ag | Fungicidal active ingredient combinations |
US6297236B1 (en) | 1998-04-06 | 2001-10-02 | Bayer Aktiengesellschaft | Fungicide active substance combinations |
US20020072535A1 (en) | 1997-04-18 | 2002-06-13 | Klaus Stenzel | Fungicide active substance combinations |
CZ299415B6 (en) * | 1997-04-25 | 2008-07-16 | Ishihara Sangyo Kaisha, Ltd. | Composition for and method of controlling harmful bio-organisms and method of enhancing activity of an agent intended for such control |
PL197250B1 (en) | 1998-05-04 | 2008-03-31 | Basf Ag | Fungicidal mixtures |
DE19904081A1 (en) | 1999-02-02 | 2000-08-03 | Bayer Ag | Fungicidal active ingredient combinations |
JP4351789B2 (en) | 1999-07-16 | 2009-10-28 | 石原産業株式会社 | Pest control composition and pest control method |
BR0016336A (en) * | 1999-12-13 | 2002-08-27 | Bayer Ag | Combinations of fungicidal active substances |
DE10021412A1 (en) * | 1999-12-13 | 2001-06-21 | Bayer Ag | Fungicidal active ingredient combinations |
JP2001181114A (en) | 1999-12-27 | 2001-07-03 | Kumiai Chem Ind Co Ltd | Agricultural and horticultural bactericide composition |
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JP2008189658A (en) * | 2007-01-12 | 2008-08-21 | Nissan Chem Ind Ltd | Method of controlling plant disease |
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CA2435364C (en) | 2010-04-20 |
PL365819A1 (en) | 2005-01-10 |
EP1355531A1 (en) | 2003-10-29 |
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CN100512645C (en) | 2009-07-15 |
CZ301672B6 (en) | 2010-05-19 |
CA2435364A1 (en) | 2002-07-25 |
IL156709A0 (en) | 2004-01-04 |
ZA200306514B (en) | 2004-09-06 |
ATE313260T1 (en) | 2006-01-15 |
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BR0206553A (en) | 2004-06-22 |
BG107980A (en) | 2004-07-30 |
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US20040053980A1 (en) | 2004-03-18 |
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SK9002003A3 (en) | 2003-12-02 |
UA74418C2 (en) | 2005-12-15 |
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